Social impact ‘stories behind the numbers’ Winnipeg-based clothing company Red Rebel Armour finalist in $50K national Indigenous Venture Challenge By: Aaron Epp Posted: 8:34 PM CST Friday, Jan. 9, 2026

Sean Rayland-Boubar is rethinking the pitch he uses to tell people about his clothing company, Red Rebel Armour.

The Winnipeg-based streetwear and custom manufacturing company was recently named one of five finalists in the Indigenous Venture Challenge, a national competition that connects Indigenous-led ventures with Indigenous angel investors.

Rayland-Boubar will be in Vancouver on Jan. 20 to make one final pitch to the 13 investors. If they choose Red Rebel Armour, the company will receive a $50,000 investment prize.

“I’m a little bit nervous about it and everything, ‘cause it’s definitely a next step,” Rayland-Boubar said. “It’s not in my home province, too, right? So it’s going to be different.”

The 38-year-old entrepreneur should feel some measure of confidence given he’s already made it this far.

The challenge started with 77 companies from across Canada. Through a structured process that included workshops and one-on-one meetings with founders, the investors narrowed the pool down to 25, 10 and now five finalists.

Red Rebel Armour is up against four B.C.-based companies: CarneBar, a protein bar business; KnowledgeKeepr, a data intelligence platform that provides up-to-date insight on all 634 First Nations in Canada; MRF FieldTech, a technology company working in the area of forestry and environmental fieldwork; and Heartberry Soda, a small-batch craft soda brand.

Making it to the top five is validation Red Rebel Armour is moving in the right direction, Rayland-Boubar said.

“The relatives keep showing up,” he said. “They want to work … And it pushes me to want to keep trying to grow (the company) as far as it (can go).”

“Relatives” is the word Rayland-Boubar uses to refer to the Indigenous people he hires.

Red Rebel Armour offers a range of ethically-sourced clothing that integrates Anishinaabe motifs into streetwear to celebrate Indigenous identity. But that isn’t the founder’s only goal for the company: he wants to reduce recidivism by offering paid on-the-job training to those re-entering the community from the criminal justice system.

“We know that you need income right away when you get released and you need a safe place to work that’s flexible,” Rayland-Boubar said. “So, that’s what we’re providing there.”

Rayland-Boubar employs three people full-time and brings on additional part-time and casual staff during busy periods.

The father of five knows what it takes to rehabilitate one’s self. He landed in prison for the first time when he was 18, and spent the next decade in and out of incarceration.

Eventually, he met an elder and their conversation turned to intergenerational trauma. It launched a journey of healing for Rayland-Boubar. He embraced his Anishinaabe roots, became a sundancer and started participating in sharing circles. He got out of the Winnipeg Remand Centre in 2018, and started Red Rebel Armour in his basement while working as a stock boy.

By 2022, the company was occupying a 300-square-foot space in the North End’s Social Enterprise Centre and doing $360,000 in annual sales. The company moved to its current production facility and storefront, a 2,300-sq.-ft. space on Century Street, in February 2023.

Red Rebel Armour hit a milestone in its last fiscal year, when it reached $1 million in sales. Rayland-Boubar’s goal for this year is to increase that number by 50 per cent.

If he wins the Indigenous Venture Challenge, he plans to use the money for inventory, marketing and to consolidate some high-interest loans.

Richard Tuck, CEO of Wakopa Financial Workers’ Co-operative in Winnipeg and a co-founder of the Indigenous Venture Challenge, said the challenge is developing Indigenous finance without colonial concepts of interest rates or equity ownership.

“What we are developing is a kinder capital rooted in relationship, long-term shared success and sustainability that lessens the power imbalance that investors have over those looking for capital,” Tuck said in an email.

The investors are looking at three main things for their decision, he added: scalable growth or revenue potential, pathway to profitability and commitment to lasting impact.

While Red Rebel Armour has an advantage because it has existed the longest of the five finalists, Tuck said, it’s the way Rayland-Boubar places social impact at the centre of his business that really makes the company shine.

“For me, Sean’s tenacity is what makes him a great entrepreneur and his commitment to impact through all his decisions makes him a great social entrepreneur,” Tuck said. “He is an icon.”

The venture challenge is part of the Indigenous Tech Conference being held at the Sheraton Vancouver Airport Hotel on Jan. 20-21. Indigenous Tech Circle, a national network advancing Indigenous leadership, innovation and investment in the technology sector, is hosting the conference.

Ryan St. Germaine, Vancouver-based founder and CEO of Indigenous Tech Circle, said he hopes the venture challenge benefits all of the finalists.

“Our hope is that it exposes everyone to, and helps people create, better businesses,” he said.

As Rayland-Boubar reworks his pitch, he’s focused on conveying to investors the journey Red Rebel Armour has been on to this point. “The stories behind the numbers — that’s what matters and that’s what I want to talk about.”

aaron.epp@freepress.mb.ca